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  • Title: Synthesis of N-(1-nitropyren-6-yl and 8-yl)-2'-deoxyribonucleosides.
    Author: Sano T, Kaya K.
    Journal: Chem Res Toxicol; 1995; 8(5):699-702. PubMed ID: 7548752.
    Abstract:
    A new type of 1-nitropyrene--DNA adduct via addition--elimination reaction was synthesized. Treatment of fluorinated 1-nitropyrene with 3'- and 5'-O-protected 2'-deoxyribonucleoside in dimethyl sulfoxide at 140 degrees C afforded N-(1-nitropyren-6-yl or 8-yl)-2'-deoxyribonucleoside. These DNA adducts resulted from addition of the exocyclic amino group of deoxynucleosides to the fluorinated carbon of the fluoro-1-nitropyrene following elimination of fluoride anion. This is the first report that describes the 1-nitropyrene-DNA adducts in which aromatic ring moiety of 1-nitropyrene is covalently linked to the exocyclic amino group of the deoxyribonucleoside. From our findings, we suggest that the addition-elimination reaction may be responsible for the formation mechanism of the putative 1-nitropyrene--DNA adducts in vivo.
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